The most compliments I ever got on a tie was on one I got at Goodwill. My most favorite armchair I found at a used furniture store. And in the late 1990s, my colleagues and clients practically drooled over my 15-year old Ford Thunderbird. Very, very often I have done just as well or better buying used instead of new. So when does it make sense to me to buy new? Here is when.
When time matters. It can take quite a while to find the right used item. In contrast, I can find a new item almost instantly googling online. So, if there isn't time -- or I do not want to make the time -- to search for used, I will go ahead and buy new.
Electronics. I do not trust used radios, computers, cameras, tvs and so on. Not unless they are so dirt cheap that I am prepared to just lose the purchase price. So if the used price is $30 or more, I buy new.
Items priced below $20. My time is worth at least $25 an hour to me. So at a $20 new item price point, searching for a cheaper used alternative is not worth it to me. My time is worth more to me that the amount I might save by searching.
Other than that, though, used items are fine with me. Used items can work just as well as new ones. They can look just as good as new ones. They can save me a lot of money that I can then put to good use on other things. And buying used helps me lead a comfortable life on a baseline budget of $18,000 a year*.
*My $18K Annual Baseline Budget: